CA2681809A1 - Imidazolidinone derivatives - Google Patents

Imidazolidinone derivatives Download PDF

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CA2681809A1
CA2681809A1 CA002681809A CA2681809A CA2681809A1 CA 2681809 A1 CA2681809 A1 CA 2681809A1 CA 002681809 A CA002681809 A CA 002681809A CA 2681809 A CA2681809 A CA 2681809A CA 2681809 A1 CA2681809 A1 CA 2681809A1
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phenyl
carbonyl
imidazolidin
piperazine
benzenesulfonyl
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CA2681809C (en
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Henrietta Dehmlow
Bernd Kuhn
Ulrike Obst Sander
Stephan Roever
Tanja Schulz-Gasch
Matthew Wright
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F Hoffmann La Roche AG
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F. Hoffmann-La Roche Ag
Henrietta Dehmlow
Bernd Kuhn
Ulrike Obst Sander
Stephan Roever
Tanja Schulz-Gasch
Matthew Wright
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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene
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    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems

Abstract

The invention is concerned with novel imidazolidinone derivatives of formula (I) wherein R 1 to R 11 and X are as defined in the description and in the claims, as well as physiologically acceptable salts thereof. These compounds bind to LXR alpha and LXR beta and can be used as medicaments.

Claims (34)

1. Compounds of formula (I) wherein X is N or CH;

R1 is lower-alkyl, fluoro-lower-alkyl, lower-alkoxy-lower-alkyl, cycloalkyl, cycloalkyl-lower-alkyl, aryl, aryl-lower-alkyl, heterocyclyl, heterocyclyl-lower-alkyl, heteroaryl or heteroaryl-lower-alkyl, wherein a cycloalkyl, aryl, heterocyclyl or heteroaryl can optionally be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, lower-alkyl, fluoro-lower-alkyl, lower-alkoxy, lower-alkoxy-lower-alkyl and fluoro-lower-alkoxy;

R2 is lower-alkyl, lower-alkoxy-lower-alkyl, halogen-lower-alkyl, lower-alkenyl, cycloalkyl, cycloalkyl-lower-alkyl, aryl, aryl-lower-alkyl, heterocyclyl, heterocyclyl-lower-alkyl, heteroaryl or heteroaryl-lower-alkyl, wherein a cycloalkyl, aryl, heterocyclyl or heteroaryl can optionally be substituted with 1 to 5 substituents independently selected from the group consisting of halogen, lower-alkyl, fluoro-lower-alkyl, lower-alkoxy and fluoro-lower-alkoxy;

R3 is aryl or heteroaryl, which aryl or heteroaryl can optionally be substituted with 1 to substituents independently selected from the group consisting of halogen, CN, lower-alkyl, fluoro-lower-alkyl, lower-alkoxy and fluoro-lower-alkoxy;

R4, R5, R6, R7, R8, R9, R10 and R11 independently from each other are hydrogen or lower-alkyl, or R4 and R5 are bound together, or R6 and R7 are bound together, or R8 and R9 are bound together, or R10 an R11 are bound together, to form a ring together with the carbon atom to which they are attached, and -R4-R5-, -R6-R7-, -R8-R9- and/or -R10-R11- is -(CH2)2-6-;

and pharmaceutically acceptable salts thereof.
2. Compounds according to claim 1, wherein X is N.
3. Compounds according to any of claims 1 - 2, wherein R1 is lower-alkyl, fluoro-lower-alkyl or phenyl, which phenyl is optionally substituted with 1 to substituents independently selected from the group consisting of halogen, lower-alkyl, fluoro-lower-alkyl, lower-alkoxy and fluoro-lower-alkoxy.
4. Compounds according to any of claims 1 - 3, wherein R1 is lower-alkyl or phenyl, which phenyl is optionally substituted with 1 to 2 substituents independently selected from the group consisting of halogen and fluoro-lower-alkyl.
5. Compounds according to any of claims 1 - 4, wherein R1 is isopropyl, 2-trifluoromethyl-phenyl, 2-chloro-phenyl or 2,3-dichloro-phenyl.
6. Compounds according to any of claims 1 - 4, wherein R1 is phenyl.
7. Compounds according to any of claims 1 - 2, wherein R1 is pyridinyl, naphthyl, cycloalkyl or cycloalkyl-lower-alkyl.
8. Compounds according to any of claims 1 - 2 or 7, wherein R1 is naphthyl.
9. Compounds according to any of claims 1 - 8, wherein R2 is lower-alkyl, lower-alkenyl, cycloalkyl or phenyl, which phenyl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen.
10. Compounds according to any of claims 1 - 9, wherein R2 is isopropyl, cyclohexyl, phenyl, 2-fluoro-phenyl, 2-chloro-phenyl or 2,4-difluoro-phenyl.
11. Compounds according to any of claims 1 - 8, wherein R2 is halogen-lower-alkyl, tetrahydropyranyl, pyridinyl or aryl-lower-alkyl.
12. Compounds according to any of claims 1 - 8 or 11, wherein R2 is benzyl.
13. Compounds according to any of claims 1 - 12, wherein R3 is phenyl or a heteroaryl selected from the group consisting of pyridinyl, 3-thieno[3,2-c]pyridin-4-yl or pyrazinyl, which phenyl or heteroaryl is optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, CN, lower-alkyl, fluoro-lower-alkyl and lower-alkoxy.
14. Compounds according to any of claims 1 - 13, wherein R3 is phenyl or pyridinyl, which phenyl or pyridinyl is optionally substituted with 1 to 2 substituents independently selected from the group consisting of halogen, lower-alkyl and fluoro-lower-alkyl.
15. Compounds according to any of claims 1 - 14, wherein R3 is 2,5-dimethyl-phenyl, 2-methyl-5-chloro-phenyl, 3-trifluoromethyl-pyridin-2-yl, 3-chloro-pyridin-2-yl or 3-bromo-6-methyl-pyridin-2-yl.
16. Compounds according to any of claims 1 - 12, wherein R3 is a heteroaryl selected from the group consisting of benzo[d]isothiazolyl, benzooxazolyl and pyrazinyl, which heteroaryl is optionally substituted with 1 to 3 substituents independently selected from lower-alkyl.
17. Compounds according to any of claims 1 - 12 or 16, wherein R3 is benzo[d]isothiazol-3-yl or 3,6-dimethyl-pyrazin-2-yl.
18. Compounds according to any of claims 1 - 17, wherein R4, R5, R6, R7, R8, R9, R10 and R11 independently are hydrogen or lower-alkyl.
19. Compounds according to any of claims 1 - 18, wherein R4, R5, R6, R7, R8, R9, R10 and R11 are hydrogen.
20. Compounds according to any of claims 1 - 19, selected from the group consisting of (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-1-(3-methoxy-benzenesulfonyl)-3-phenyl-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(3-Methoxy-benzenesulfonyl)-4-[4-(2-methoxy-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(3-Methoxy-benzenesulfonyl)-3-phenyl-4-[4-(3-trifluoromethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-(3-Methoxy-benzenesulfonyl)-3-phenyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-(3-Methoxy-benzenesulfonyl)-4-[4-(3-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(3-Methoxy-benzenesulfonyl)-4-[4-(2-methoxy-phenyl)-piperidine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-3-(2-Chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one, (RS)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-(2-chloro-phenyl)-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(toluene-4-sulfonyl)-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-2-{4-[2-Oxo-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidine-carbonyl]-piperazin-1-yl}-benzonitrile, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-ethyl-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-isopropyl-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-propyl-imidazolidin-2-one, (RS)-3-Allyl-1-benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-butyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclopentyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (R)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-(2-fluoro-phenyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(3-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(4-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-(4-fluoro-phenyl)-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-(4-fluoro-phenyl)-imidazolidin-2-one, (S)-1-Benzenesulfonyl-3-(2,4-difluoro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-benzyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl] -imidazolidin-2-one, (+)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-(2-chloro-phenyl)-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one, (-)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-(2-chloro-phenyl)-1-(3-methoxy-benzenesulfonyl)-imidazolidin-2-one, (RS)-1-(3-Chloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(2-Chloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(2,4-Difluoro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(3,3,3-trifluoro-propane-1-sulfonyl)-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-1-(Butane-1-sulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-cyclohexyl-imidazolidin-2-one, (RS)-2-[4-(1-Benzenesulfonyl-3-cyclohexyl-2-oxo-imidazolidine-4-carbonyl)-piperazin-1-yl]-nicotinonitrile, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-(4-pyridin-2-yl-piperazine-1-carbonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(5-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(6-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-6-[4-(1-Benzenesulfonyl-3-cyclohexyl-2-oxo-imidazolidine-4-carbonyl)-piperazin-1-yl]-nicotinonitrile, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-(4-thieno[3,2-c]pyridin-4-yl-piperazine-carbonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(3,5-dichloro-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-3-Phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-4-[4-(3-Chloro-5-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(3-bromo-6-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-cyclohexyl-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(4-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-2-[4-(1-Benzenesulfonyl-3-cyclohexyl-2-oxo-imidazolidine-4-carbonyl)-piperazin-1-yl]-6-methyl-nicotinonitrile, (RS)-1-(2,3-Dichloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(2,5-Dichloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-1-(2-fluoro-benzenesulfonyl)-3-phenyl-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-1-(3-fluoro-benzenesulfonyl)-3-phenyl-imidazolidin-2-one, (RS)- 1-(3-Chloro-2-fluoro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(3-Difluoromethoxy-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(3-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-(3',6'-dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(3-chloro-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-(2,5-Difluoro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-1-(2,6-Dichloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, and (S)-1-benzenesulfonyl-3-benzyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one and pharmaceutically acceptable salts thereof.
21. Compounds according to any of claims 1 - 20, selected from the group consisting of (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-4-[4-(5-Chloro-2-methyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-isopropyl-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-(2-fluoro-phenyl)-imidazolidin-2-one, (S)-1-Benzenesulfonyl-3-(2,4-difluoro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-(2-Chloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, (RS)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-cyclohexyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-[4-(3-bromo-6-methyl-pyridin-2-yl)-piperazine-1-carbonyl]-3-cyclohexyl-imidazolidin-2-one, (RS)-1-(2,3-Dichloro-benzenesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, and (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-[4-(3-chloro-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, and pharmaceutically acceptable salts thereof.
22. Compounds according to any of claims 1 - 19, selected from the group consisting of (RS)-1-Benzenesulfonyl-4-(4-benzo[d]isothiazol-3-yl-piperazine-1-carbonyl)-3-(2-chloro-phenyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-4-(4-benzooxazol-2-yl-piperazine-1-carbonyl)-3-(2-chloro-phenyl)-imidazolidin-2-one, 4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-1-(pyridine-2-sulfonyl)-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-(2-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-(2-chloro-phenyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-propyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, 1-Benzenesulfonyl-3-cyclohexyl-4-[(R)-2-methyl-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, 1-Benzenesulfonyl-3-cyclohexyl-4-[(S)-2-methyl-4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-isopropyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-3-Butyl-1-(2-chloro-benzenesulfonyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-(3-iodo-propyl)-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-cyclopropyl-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-(tetrahydro-pyran-4-yl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-4-(3',6'-Dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-1-Benzenesulfonyl-3-(2-chloro-phenyl)-4-(3',6'-dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-imidazolidin-2-one, (RS)-3-(2,4-Difluoro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-3-(2,4-Difluoro-phenyl)-4-(3',6'-dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-4-[4-(3-Chloro-pyridin-2-yl)-piperazine-1-carbonyl]-3-(2,4-difluoro-phenyl)-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-3-(2-Chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-3-(2-Chloro-phenyl)-4-(3',6'-dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-1-(propane-2-sulfonyl)-imidazolidin-2-one, (RS)-3-(2-Chloro-phenyl)-4-[4-(3-chloro-pyridin-2-yl)-piperazine-1-carbonyl]-1-(propane-2-sulfonyl)-imidazolidin-2-one, (S)-3-Benzyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(naphthalene-sulfonyl)-imidazolidin-2-one, (S)-4-[4-(2,5-Dimethyl-phenyl)-piperazine-1-carbonyl]-1-(naphthalene-1-sulfonyl)-3-propyl-imidazolidin-2-one, (S)-1-Benzenesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-pyridin-2-yl-imidazolidin-2-one, (S)-3-Benzyl-1-cyclopropanesulfonyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S) -3-Benzyl-1-(cyclohexylmethanesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, and (S) -1-(Cyclohexylmethanesulfonyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-3-phenyl-imidazolidin-2-one, and pharmaceutically acceptable salts thereof.
23. Compounds according to any of claims 1-19 or 22, selected from the group consisting of (RS)-1-Benzenesulfonyl-4-(4-benzo[d]isothiazol-3-yl-piperazine-1-carbonyl)-3-(2-chloro-phenyl)-imidazolidin-2-one, (S)-1-(2-Chloro-benzenesulfonyl)-3-(2-chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-imidazolidin-2-one, (S) -1-(2-Chloro-benzenesulfonyl)-3-(2-chloro-phenyl)-4-[4-(3-trifluoromethyl-pyridin-2-yl)-piperazine-1-carbonyl]-imidazolidin-2-one, (RS)-4-(3',6'-Dimethyl-2,3,5,6-tetrahydro-[1,2']bipyrazinyl-4-carbonyl)-3-phenyl-1-(2-trifluoromethyl-benzenesulfonyl)-imidazolidin-2-one, (RS)-3-(2-Chloro-phenyl)-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(propane-2-sulfonyl)-imidazolidin-2-one, and (S)-3-Benzyl-4-[4-(2,5-dimethyl-phenyl)-piperazine-1-carbonyl]-1-(naphthalene-sulfonyl)-imidazolidin-2-one, and pharmaceutically acceptable salts thereof.
24. A process for the manufacture of compounds of formula (I) as defined in any of claims 1-23, which process comprises a) reacting a compound of formula (II) with a compound of formula (III) or b) reacting a compound of formula (IV) with a compound R2NCO, or c) reacting a compound of formula (V) with a compound R1SO2Cl, or d) reacting a compound of formula (VI) with a compound R2LG, wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and X are as defined in any of claims 1-23 and LG is a leaving group.
25. Compounds according to any of claims 1 - 23, when manufactured by a process according to claim 24.
26. Pharmaceutical compositions comprising a compound according to any of claims 1 - 23 and a pharmaceutically acceptable carrier and/or adjuvant.
27. Compounds according to any of claims 1 - 23 for use as therapeutic active substances.
28. Compounds according to any of claims 1 - 23 for use as therapeutic active substances for the treatment and/or prophylaxis of diseases which are modulated by LXR
alpha and/or LXR beta agonists.
29. A method for the therapeutic and/or prophylactic treatment of diseases which are modulated by LXR alpha and/or LXR beta agonists, particularly for the therapeutic and/or prophylactic treatment of increased lipid levels, increased cholesterol levels, low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, sepsis, inflammatory diseases, infectious diseases, skin diseases, colitis, pancreatitis, cholestasis of the liver, fibrosis of the liver, psoriasis, Alzheimer's disease, impaired/improvable cognitive function, HIV, cancer, age related forms of macular degeneration, inherited forms of macular degeneration and/or Stargadt's disease, which method comprises administering a compound according to any of claims 1 - 23 to a human being or animal.
30. The use of compounds according to any of claims 1 - 23 for the therapeutic and/or prophylactic treatment of diseases which are modulated by LXR alpha and/or LXR
beta agonists.
31. The use of compounds according to any of claims 1-23 for the therapeutic and/or prophylactic treatment of increased lipid levels, increased cholesterol levels, low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, sepsis, inflammatory diseases, infectious diseases, skin diseases, colitis, pancreatitis, cholestasis of the liver, fibrosis of the liver, psoriasis, Alzheimer's disease, impaired/improvable cognitive function, HIV, cancer, age related forms of macular degeneration, inherited forms of macular degeneration and/or Stargadt's disease.
32. The use of compounds according to any of claims 1-23 for the preparation of medicaments for the therapeutic and/or prophylactic treatment of diseases which are modulated by LXR alpha and/or LXR beta agonists.
33. The use of compounds according to any of claims 1- 23 for the preparation of medicaments for the therapeutic and/or prophylactic treatment of increased lipid levels, increased cholesterol levels, low HDL-cholesterol, high LDL-cholesterol, atherosclerotic diseases, diabetes, non-insulin dependent diabetes mellitus, metabolic syndrome, dyslipidemia, sepsis, inflammatory diseases, infectious diseases, skin diseases, colitis, pancreatitis, cholestasis of the liver, fibrosis of the liver, psoriasis, Alzheimer's disease, impaired/improvable cognitive function, HIV, cancer, age related forms of macular degeneration, inherited forms of macular degeneration and/or Stargadt's disease.
34. The invention as hereinbefore defined.
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